Learning objectives
Chimica Organica Propedeutica
Aim of the course is to introduce the basic and general concepts of organic chemistry.
Chimica Organica
The course is aimed at developing knowledge and concepts rooted in the “Propedeutic Organic Chemistry” course, with a particular emphasis on the structure-activity relationship of the main organic compounds.
Prerequisites
Chimica Organica Propedeutica
To access the final examination, it is necessary to having successfully passed the following examination: General and Inorganic Chemistry.
Chimica Organica
To access the final examination, it is necessary to having successfully passed the following examinations: General and Inorganic Chemistry, Propedeutic Organic Chemistry module.
Course unit content
Chimica Organica Propedeutica
General.
Origin and development of organic chemistry as a science. Functional groups of the main organic compounds. The carbon atom as a focal element in organic chemistry. Relationships between the structure of an organic compound and its physical and chemical behaviour. Hybridation,molecular geometry, electronegativity, polarity of organic compounds. Resonance of organica compounds. resonance, Configurational and conformational isomerism. Conformational analysis of linear and cyclic alkanes. Constitutional isomerism and stereoisomerism. Chirality, enantiomers, diastereoisomers, meso compounds, geometric isomerism. Thermodynamic and kinetic control of organic reactions. Reaction kinetics, activation energy, catalysis. Reaction mechanisms. Resonance in organic compounds. Radical and ionic reactions. Nucleophilic and electrophilic species. Acidity and basicity in organic chemistry, acid-base reactions. Oxidative-reductive reactions. Monomolecular and bimolecular nucleophilic substitutions at saturated carbons. Monomolecular and bimolecular beta-elimination reactions. Main solvents and their use in organic chemistry. Organometallic reagents, Grignard reagents. Electrophilic additions to alkenes and alkynes. Regioselective, stereospecific, and stereoselective organic reactions.
Aliphatic domain. Structure, nomenclature, natural occurrence, physical properties, reactivity, and synthesis of the following compound classes: alkanes, cycloalkanes, alkyl halides, alkenes, alkynes, alcohols, polyols, thiols.
Chimica Organica
General.
Recall and in-depth study of the contents acquired in the previous “Propedeutic Organic Chemistry” course. Nucleophilic addition to carbon-oxygen double bond. Acyl nucleophilic substitution. Brief description of the role of protecting groups in organic synthesis. Qualitative identification of the main functional groups. Carbon-carbon bond-forming reactions. Synthesis of enols and enolates, imines and enamines. Alpha-alkylation and alpha-halogenation of enols and enolates. Aldol additions and condensations and variants thereof. Claisen condensations and related reactions. Michael and Mannich addition reactions. Examples of transposition reactions.
Aliphatic domain. Structure, nomenclature, natural occurrence, physical properties, reactivity, and synthesis of the following compound classes: ethers, epoxides, aldehydes, ketones, carboxylic acids, acyl halides, anhydrides, esters, thioesters, lactones, amides, lactams., imides, nitriles, 1,3-dicarbonyl compounds, alpha,beta-unsaturated compounds, amines, nitro- and nitroso-derivatives, azo-compounds.
Aromatic domain. Aromaticity. Structure, nomenclature, natural occurrence, physical properties, reactivity, and synthesis of the following compound classes: benzene, substituted benzenes and, in particular, phenols, aryl halides, and aromatic amines.
Full programme
Chimica Organica Propedeutica
General.
Origin and development of organic chemistry as a science. Functional groups of the main organic compounds. The carbon atom as a focal element in organic chemistry. Relationships between the structure of an organic compound and its physical and chemical behaviour. Hybridation,molecular geometry, electronegativity, polarity of organic compounds. Resonance of organica compounds. resonance, Configurational and conformational isomerism. Conformational analysis of linear and cyclic alkanes. Constitutional isomerism and stereoisomerism. Chirality, enantiomers, diastereoisomers, meso compounds, geometric isomerism. Thermodynamic and kinetic control of organic reactions. Reaction kinetics, activation energy, catalysis. Reaction mechanisms. Resonance in organic compounds. Radical and ionic reactions. Nucleophilic and electrophilic species. Acidity and basicity in organic chemistry, acid-base reactions. Oxidative-reductive reactions. Monomolecular and bimolecular nucleophilic substitutions at saturated carbons. Monomolecular and bimolecular beta-elimination reactions. Main solvents and their use in organic chemistry. Organometallic reagents, Grignard reagents. Electrophilic additions to alkenes and alkynes. Regioselective, stereospecific, and stereoselective organic reactions.
Aliphatic domain. Structure, nomenclature, natural occurrence, physical properties, reactivity, and synthesis of the following compound classes: alkanes, cycloalkanes, alkyl halides, alkenes, alkynes, alcohols, polyols, thiols.
Chimica Organica
General.
Recall and in-depth study of the contents acquired in the previous “Propedeutic Organic Chemistry” course. Nucleophilic addition to carbon-oxygen double bond. Acyl nucleophilic substitution. Brief description of the role of protecting groups in organic synthesis. Qualitative identification of the main functional groups. Carbon-carbon bond-forming reactions. Synthesis of enols and enolates, imines and enamines. Alpha-alkylation and alpha-halogenation of enols and enolates. Aldol additions and condensations and variants thereof. Claisen condensations and related reactions. Michael and Mannich addition reactions. Examples of transposition reactions.
Aliphatic domain. Structure, nomenclature, natural occurrence, physical properties, reactivity, and synthesis of the following compound classes: ethers, epoxides, aldehydes, ketones, carboxylic acids, acyl halides, anhydrides, esters, thioesters, lactones, amides, lactams., imides, nitriles, 1,3-dicarbonyl compounds, alpha,beta-unsaturated compounds, amines, nitro- and nitroso-derivatives, azo-compounds.
Aromatic domain. Aromaticity. Structure, nomenclature, natural occurrence, physical properties, reactivity, and synthesis of the following compound classes: benzene, substituted benzenes and, in particular, phenols, aryl halides, and aromatic amines.
Bibliography
Essential texts (choose one of the following):
1. W.H. Brown, C.S. Foote, B. L. Iverson, E. V. Anslyn, “Chimica Organica”, IV Edizione, EdiSES, Napoli, 2010.
2. Autori vari, “Chimica Organica” (a cura di B. Botta), Edi.Ermes, Milano, 2011.
3. J. McMurry, “Chimica Organica”, VIII Edizione, Piccin, Padova, 2012.
4. M. Loudon, “Chimica Organica”, V Edizione, EdiSES, Napoli, 2010.
5. J. G. Smith, "Chimica Organica", McGraw-Hill, Milano, 2007.
6. G.H. Schmid, “Chimica Organica”, Casa Editrice Ambrosiana, Milano, 1997.
Essential bibliography (choose one of the following excercize books):
1. M. V. D’Auria, O. Taglialatela Scafati, A. Zampella, “Guida Ragionata allo Svolgimento di Esercizi di Chimica Organica”, seconda Edizione, Loghia Ed., Napoli, 2011.
2. B. Iverson, S. Iverson, “Guida alla soluzione dei problemi da Brown, Foote, Iverson – Chimica Organica”, 3° Ed., EdiSES, Napoli, 2006.
3. T.W.G. Solomons, C.B. Fryhle, R.G. Johnson, “La chimica organica attraverso gli esercizi”, Seconda Edizione, Zanichelli, Bologna, 2010.
4. S. Cacchi, F. Nicotra, “Esercizi di Chimica Organica”, Casa Editrice Ambrosiana, Milano, 1998.
Bibliography for consultation:
1. J. Clayden, N. Greeves, S. Warren, P. Wothers, “Organic Chemistry”, Oxford Edition, 2001.
2. R. Norman, J.M. Coxon, “Principi di Sintesi Organica”, 2a Edizione Italiana, Piccin Editore, Padova, 1997.
3. R.T. Morrison, R.N. Boyd, “Chimica Organica”, VI Edizione, Casa Editrice Ambrosiana, 1997.
Other teaching material: Examples of exercizes of examinations of previous years.
Teaching methods
Chimica Organica Propedeutica
The course is carried out through frontal oral lessons comprising exercises.
Chimica Organica
The course is carried out through frontal oral lessons comprising exercises.
Assessment methods and criteria
Chimica Organica Propedeutica
The final examination consists of a written exam. The written exam deals with the execution of exercises on the synthesis and reactivity of organic compounds. The exam is intended to test and confirm the student knowledge on the matter.
Chimica Organica
The final examination consists of a written exam and an oral colloquium (only if the written exam has been passed). The written exam deals with the execution of exercises on the synthesis and reactivity of organic compounds. The oral colloquium is intended to test and confirm the student knowledge on the matter.
Other information
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